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134910

Sigma-Aldrich

(1R,2S)-(−)-Ephedrine

98%

Synonyme(s) :

(−)-Ephedrine, (1R,2S)-(−)-α-(1-Methylaminoethyl)benzyl alcohol, (1R,2S)-(−)-2-Methylamino-1-phenyl-1-propanol, L-α-(1-Methylaminoethyl)benzyl alcohol

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About This Item

Formule linéaire :
C6H5CH[CH(NHCH3)CH3]OH
Numéro CAS:
299-42-3
Poids moléculaire :
165.23
Beilstein:
2208730
Numéro CE :
206-080-5
Numéro MDL:
MFCD00064257
Code UNSPSC :
12352116
ID de substance PubChem :
24848190
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

98%

Forme

solid

Activité optique

[α]21/D −41°, c = 5 in 1 M HCl

pb

255 °C (lit.)

Pf

37-39 °C (lit.)

Densité

1.124 g/mL at 25 °C (lit.)

Groupe fonctionnel

amine
hydroxyl
phenyl

Température de stockage

2-8°C

Chaîne SMILES 

CN[C@@H](C)[C@H](O)c1ccccc1

InChI

1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

Clé InChI

KWGRBVOPPLSCSI-WPRPVWTQSA-N

Catégories apparentées

Description générale

(1R,2S)-(-)-Ephedrine, a chiral β-amino alcohol, is commonly used as a chiral auxiliary in asymmetric synthesis.[1] It undergoes reduction to form (+)-methamphetamine.[2]

Application

(1R,2S)-(-)-Ephedrine can be used in the preparation of optically active phosphine-phosphonite ligands[3] and chirally-substituted cyclopentadienyl (Cp) ligands.[4] It reacts with phosphorus trichloride to form (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine.[5] It can also act as a chiral resolving agent for (±)-mandelic acid.[6]
Versatile chiral synthon,[7] employed in catalysis[8] and in the preparation of optically pure sulfoxides[9] and oxazolidines.[10]

Pictogrammes

CorrosionExclamation mark
GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H314,H317

Classification des risques

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

186.8 °F - closed cup

Point d'éclair (°C)

86 °C - closed cup

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
STBJ7974
STBG4818V
STBG2435V
STBF3993V
STBF0862V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

A novel nucleoside phosphoramidite synthon derived from 1R, 2S-ephedrine
Iyer RP, et al
Tetrahedron Asymmetry, 6(5), 1051-1054 (1995)
A L Carey et al.
Diabetologia, 56(1), 147-155 (2012-10-16)
Brown adipose tissue (BAT) activation increases energy consumption and may help in the treatment of obesity. Cold exposure is the main physiological stimulus for BAT thermogenesis and the sympathetic nervous system, which innervates BAT, is essential in this process. However
Tetrahedron Letters, 32, 5885-5885 (1991)
Enantiomeric Resolution of (?)-Mandelic Acid by (1R, 2S)-(-)-Ephedrine. An Organic Chemistry Laboratory Experiment Illustrating Stereoisomerism
Baar MR and Cerrone-Szakal AL
Journal of Chemical Education, 82(7), 1040-1040 (2005)
New chiral phosphine-phosphonites derived from (2R, 3R)-dimethyl tartrate,(S)-binaphthol and (1R, 2S)-ephedrine
Schull TL and Knight DA
Tetrahedron Asymmetry, 10(2), 207-211 (1999)
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Chromatograms

application for HPLCapplication for HPLC

Questions

1–2 sur 2 questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 réponse

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 réponse

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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